Pioneer Courthouse Square, Portland: Our most recommended tours and activities

Portland, Oregon: Soul of the City Walking Tour

Portland, Oregon: Soul of the City Walking Tour

Discover some of Portland's most influential architecture, from cast iron-fronted structures to the grandly disastrous post-modern Portland Building, on this walking tour. Discuss the modern rise of radical activists, and how it is connected to the city’s history going back more than a century. Meet your guide in the center of the city, at Director Park, only a block from the city's Cultural District. Walk through the South Park Blocks, visiting the plazas connected to museums and concert halls, including the Portland Art Museum and the Oregon Historical Society. Explore how Portland got its nicknames and city layout, how its cultural identity was forged, and where its commitment to racial justice and social progressivism comes from. Be surprised as you find out how the state of Oregon was founded and why. Next, meet Portlandia, the image personifying the city. Learn how much of the city as you see it today has hippies to thank for its richness. End the tour at Pioneer Courthouse Square. On days when attractions are open, you can briefly enter 1 or 2 buildings. Along the way, discover what led to the prioritization of parks throughout the city center, how the city’s early urban planners decided on their layouts, how modern designers look at the past and plan for the future, and who the streets are named after.

Portland: Guided Delicious Donut Tour with Tastings

Portland: Guided Delicious Donut Tour with Tastings

Accompany your passionate foodie guide to 4 donut institutions, where you'll enjoy a curated sample of Portland's best donuts. Savor classics like glazed and chocolate, and discover some more adventurous flavors, like lavender.  Your stops may include Sesame Donuts, Blue Star Donuts, Voodoo Doughnuts and more. You'll even be able to skip the line at Voodoo Doughnuts, where some people wait up to 30 minutes. On the way to the donut shops, visit some local sights including Pioneer Square, Chinatown, and the PSU Campus. Your tour guide will entertain you with interesting facts about these sites as you travel between treats.

Portland: Food Walking Tour

Portland: Food Walking Tour

Explore downtown Portland on an all-inclusive walking food tour through the heart of the city. We'll meet at "Portland's Living Room," Pioneer Courthouse Square, and venture deeper into downtown while sampling food from unique vendors. Enjoy a philosophical introduction to Portland's iconic food cart ecosystem while learning about our city's history, culture, and people. On our tour we'll walk through the neighborhoods of downtown, old town, and chinatown, while passing through the largest independent bookstore in the world, our scenic waterfront park, and the famous Saturday Market (weekends only). Come hungry.

Portland: Afternoon City Highlights Tour

Portland: Afternoon City Highlights Tour

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown and the surrounding area. You will experience the best Portland sites including the International Rose Garden (May through mid-October), the World Forestry Museum mid-October through the end of April on Thursday, Friday, Saturday, and Sunday, the Oregon Society of Artists from mid-October through the end of April on Monday, Tuesday, and Wednesday, Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, Lake Oswego Square (seasonally), and the South Park Blocks. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer. Let the fragrance of roses embrace your senses with over 600 roses and be delighted with the beautiful Washington Park nature, featuring some of the most amazing city & mountain views around. More than 10,000 individual rose bushes bloom in the International Rose Test Garden from late May through October, representing over 610 different rose varieties. At the World Forestry Museum you can explore forests around the world through two floors of unique hands-on exhibits. The Discovery Museum’s colorful and thoughtful exhibits include information about tree planting, wildlife, the benefits of wood, outdoor recreation, and forest careers. The Oregon Society of Artists promotes visual arts in the diverse communities of our region, with educational opportunities for artists at all levels of accomplishment. While here, we will visit the OSA Gallery which changes exhibits every month, learn about the amazing history of the OSA (which started in 1926), and view rarely seen works of art by master painters who are part of the amazing history of this important part of the Portland Community. You will be taken through NW 23rd Avenue which is the heart of the Nob Hill District and is filled with century-old Victorian and Craftsman-style storefronts housing unique boutiques alongside national retailers, interspersed with coffee shops and on-trend restaurants and bars. In short, it’s a shopper’s and diners paradise. Portland’s Pearl District is the realization of a big dream. What was once a largely abandoned industrial district is now one of the most vibrant neighborhoods in the city. Scattered throughout, you will find cobblestone streets, loading docks, and lofty buildings that offer a glimpse into the district’s grittier past. It is an urban renaissance with its own unique blend of artistry, productivity, and public parks like Tanner Springs Park.

Portland: Downtown Food Tour

Portland: Downtown Food Tour

Come eat with us! Explore downtown Portland in then morning or the afternoon. Some of our city’s biggest eating trends started here, from farm-to-table restaurants to PDX’s original food cart pod, making downtown an eater's delight. Come taste the very best of what Portland’s becoming known for, including fine dining, farm-to-table, ground-breaking food halls, delicious brews, wines, cocktails, and more! One this tour we will explore the full spectrum of Portland’s food scene. Our Downtown Portland Food Tour will last approximately 2.5 hrs, and our guides will lead you on a delicious 1.5 mile jaunt through downtown! Our curated approach to this culinary experience will ensure that, you’ll get a taste of what makes our city so special. Enjoy this excursion through the historic districts, waterfront, and sites of downtown Portland - and come hungry!

Portland: Half Day City Sightseeing Tour

Portland: Half Day City Sightseeing Tour

Enjoy a fascinating and informative narration by your guide highlighting the colorful past and present of Portland’s many historic churches, diverse modern architectural wonders, abundant city parks, bountiful boutiques and world famous culinary hot spots. Highlights also include a stunning stroll through the oldest International Rose Test Garden in the entire United States and a walk through the ornate grounds of the historic Pittock Mansion, built in an impressive French Renaissance nouveau style by one of Portland’s first titans of industry. Participants will enjoy sweeping views of the Portland city skyline, surrounding snow-capped volcanoes, lush evergreen forests, charming neighborhoods, dynamic downtown and myriad displays of artwork encompassing an array of vivid murals and iconic statues.

Portland: Morning City Highlights Tour

Portland: Morning City Highlights Tour

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown and the surrounding area. You will experience the best Portland sites including the International Rose Garden (May through mid-October), the World Forestry Museum mid-October through the end of April on Thursday, Friday, Saturday, and Sunday, the Oregon Society of Artists from mid-October through the end of April on Monday, Tuesday, and Wednesday, Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, Lake Oswego Square (seasonally), and the South Park Blocks. Let the fragrance of roses embrace your senses with over 600 roses and be delighted with the beautiful Washington Park nature, featuring some of the most amazing city & mountain views around. More than 10,000 individual rose bushes bloom in the International Rose Test Garden from late May through October, representing over 610 different rose varieties. At the World Forestry Museum you can explore forests around the world through two floors of unique hands-on exhibits. The Discovery Museum’s colorful and thoughtful exhibits include information about tree planting, wildlife, the benefits of wood, outdoor recreation, and forest careers. The Oregon Society of Artists promotes visual arts in the diverse communities of our region, with educational opportunities for artists at all levels of accomplishment. While here, we will visit the OSA Gallery which changes exhibits every month, learn about the amazing history of the OSA (which started in 1926), and view rarely seen works of art by master painters who are part of the amazing history of this important part of the Portland Community. You will be taken through NW 23rd Avenue which is the heart of the Nob Hill District and is filled with century-old Victorian and Craftsman-style storefronts housing unique boutiques alongside national retailers, interspersed with coffee shops and on-trend restaurants and bars. In short, it’s a shopper’s and diners paradise. Portland’s Pearl District is the realization of a big dream. What was once a largely abandoned industrial district is now one of the most vibrant neighborhoods in the city. Scattered throughout, you will find cobblestone streets, loading docks, and lofty buildings that offer a glimpse into the district’s grittier past.

Portland: City Highlights Exploration Game

Portland: City Highlights Exploration Game

Your adventure starts at City Hall in downtown Portland. Begin your first adventure in the app and successfully complete the challenges to unlock more whacky stories and discover more locations. Unlock stories about the Shanghai Tunnels, through which unsuspecting visitors were kidnapped and carried to sea, or the Portland Hotel, where dismembered bodies were dumped. Uncover Skidmore Fountain, which would’ve run with beer instead of water if civic leaders had a sense of fun. In another story, you embark on an adventure to the leprechaun colony in Mill Ends Park from which a pot of gold has been stolen by Portland’s famous peregrine falcons. As an Irish treasure hunter, it’s your job to track it down.

Portland: Sightseeing Tour with Columbia Gorge Waterfalls

Portland: Sightseeing Tour with Columbia Gorge Waterfalls

On this full-day tour, you’ll see the best of Portland and the surrounding area and the Columbia River Gorge. Along the way, learn about Portland’s interesting history and modern-day culture from your guide. This tour combines some of the most iconic and unique places in Portland with the natural beauty and splendor of the waterfalls, scenic vistas, and historical sites in the Columbia River Gorge. More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden (seasonally), the World Forestry Museum (seasonally), the Oregon Society of Artists (seasonally), Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, Lake Oswego Square (seasonally), and the South Park Blocks. Today Portland is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer. Your Gorge adventure will take place along the Historic Columbia River National Scenic Byway, where some of the locations we may stop include, Portland Women’s Forum, Crown Point Vista House, Latourell Falls, Multnomah Falls, and Shepperd’s Dell. Millions of years ago, during the formation of the Cascade Mountain Range, lava and other pyroclastic matter flowed west from what would be the Cascades all the way to the Pacific Ocean, creating a thick shell of basalt rock that covered Western Oregon. Then, during the Pleistocene Ice Age, roughly 15,000 years ago, water from the Lake Missoula Flood carved out the Columbia River Gorge as hundreds of cubic miles of water, ice, rock and mud rushed from present-day Montana to the Pacific Ocean. Explore the beauty of the canyon walls and rock formations, breathtaking waterfalls and awe-inspiring visas that make the Columbia River National Scenic Area one of the Seven Wonders of Oregon. Our enthusiastic guides will introduce you to the most amazing places in the Gorge while providing a comprehensive narrative of this spectacular landscape and its transformative history.

Portland: Smart Phone Scavenger Hunt

Portland: Smart Phone Scavenger Hunt

Turn Portland into a giant game board on a smart phone operated scavenger hunt of the city, and discover the sights from a new perspective! The interactive hunt combines all the fun of the “Amazing Race” with a sightseeing tour of some of the city’s most historic areas. Let your smart phone guide you past well-known attractions and overlooked gems, solving clues and completing challenges as you go. Start on Pioneer Courthouse Square and continue to the Arts District. See Art Deco theaters and riverside panoramas as you pass sights such as the Portland Art Museum, statue of Portlandia, Ira Keller Fountain Park, and Powells Books, flagship store of the largest independent bookstore chain in the world! The route covers approximately 2.4 miles, and lets you experience Portland’s famous street cars along the way. You can start when you want, and determine your own pace of play. Stop for lunch, take in the sights, or grab a bite at Voodoo Donuts - “the magic is in the hole!” Tours are set at a fixed price for a group versus per person pricing, so this is the perfect city adventure for groups who want to get the best bang for their buck.

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Things to Do in Pioneer Courthouse Square, Portland

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What people are saying about Pioneer Courthouse Square, Portland

Overall rating

4.7
(11 reviews)

Fun and informative tour! Our guide Nancy was knowledgeable about a variety of topics relevant to Portland's history, and pointed out interesting architecture, murals and sculptures throughout the walk. She was also a Portland native, which was a great bonus.

Really great overview of the downtown and Pearl districts. Shannon was super knowledgeable and friendly. It was just the two of us along with guide that day so it all felt really personalized. Highly recommended.

David was amazing. We had 6 or 7 stops and everything was so yummy and enjoyable. really showed us Portland with a lot of information and history. Book it if you can!

Great tour of the city, with wonderful commentary about its history from Nancy our tour guide.

The tour was wonderful; Dave is passionate, knowledgeable and humorous!